The present invention is a process specific for the preparation of bis- and tris-amines by the contact of silylorganoamines with palladium monoxide catalyst. The process results in near quantitative conversion of the silylorganoamines to the desired bis- and tris-amines, without the need for elevated pressures and without formation of salts of ammonia and chloride.
The bis- and tris-amines formed by the present process are particularly useful as adhesion promoting agents for glass and other materials. These amines also have wide applications for fabric treatment and in personal care products.
Speier, U.S. Pat. No. 2,715,133, issued Aug. 9, 1955, describes a process for the preparation of organosilylmethylamines. The process involves heating a halogenomethylsilane with ammonia or an amine under pressure. The process is reported to produce the corresponding aminomethylsilane and the bis- derivative thereof.
Jex et al., U.S. Pat. No. 2,832,754, issued Apr. 29, 1958, provides a process for preparing trialkoxysilylpropylamine and the bis- and tris- derivatives thereof. The process involves reacting ammonia with gammachloropropyltrialkoxysilane, where the ammonia is present at molar excess, at a temperature of at least 90.degree. C. and at a pressure above atmospheric pressure. The process is reported to result in about a 20 to 50 percent yield of the mono(alkoxysilylpropyl)amine. A by-product of this process is typically a salt of ammonia and chloride.
Jex et al., U.S. Pat. No. 2,920,095, issued Jan. 5, 1960, describes a process for the preparation of tris(alkoxysilylpropyl)amines. The process consists of reacting a gamma-chloropropylalkoxysilane with ammonia, under pressure, at elevated temperatures. Jex reports the proportion of the mono-, bis-, and tris(alkoxysilylpropyl)amines obtained by the reaction can be controlled by the use of varying amounts of ammonia. The smaller the mole fraction of ammonia, based on the amount of gamma-chloropropylalkoxysilane in the reactants employed, the greater the proportion of the tris(alkoxysilylpropyl)amine in the product. A by-product of this process is a salt of ammonia and chloride.
It is an objective of the present invention to provide a process which results in near quantitative conversion of silylorganoamines to the corresponding bis- and tris- amines. Furthermore, it is an objective of the present invention to provide a process that can be run at atmospheric pressure and does not result in the production of salts of ammonia and chloride.